


Solving the Riddle Riddle

by Fribsnizzle



Category: Harry Potter - J. K. Rowling
Genre: Bestiality, Cunnilingus, Explicit Sexual Content, F/F, F/M, Group Sex, Lesbian Sex, Masturbation, Multi, Murder, Oral Sex, Other, Pregnancy, Sex, Underage Sex, Unplanned Pregnancy, Vaginal Sex, Voyeurism
Language: English
Status: Completed
Published: 2020-02-20
Updated: 2020-02-20
Packaged: 2021-02-27 21:04:45
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 5,248
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22812037
Author URL: https://archiveofourown.org/users/Fribsnizzle/pseuds/Fribsnizzle
Summary: Helena Ravenclaw spills what she has seen and knows about the life of young Tom Riddle and his secret exploits, including a 'harem'. But wait, there is more involving Myrtle Warren.
Relationships: Moaning Myrtle/Tom Riddle, Other Relationship Tags to Be Added
Comments: 1
Kudos: 22





	1. The Early Days

Tom Riddle, or Lord Voldemort as he would come to be known throughout the magical world, is the ultimate enigma of modern magical times. A loner who publically never made a single friend during his days at Hogwarts, his background and personal life remains as sketchy today as it did during his life.  
  
Many wonder how a quiet orphan grew up to be one of, if not the most powerful dark wizard of all time. What made him tick? What were his dreams as a child? Did he want friends and maybe even a romantic relationship? Or were his aspirations always to become immortal and take control over the world?  
  
I cannot answer all of those questions, but I can shed a little light on some of them. I am Helena Ravenclaw, sometimes referred to as the Grey Lady or the Ghost of Ravenclaw Tower. I detest those nicknames and prefer only Helena. If you wish to continue, please call me Helena.  
  
You see, or maybe do not see, that as a ghost, I have a unique ability to watch things while undetected. There are more than a few stories I can tell about events and happenings here at Hogwarts. I have never before spoken about the things I have seen, but having come to trust Harry Potter has caused me to rethink my silences and open up about a few things. So please do not think of me as some kind of pervert as I tell this story. Just consider that after nearly 1000 years as a ghost one can become willing to partake of nearly any kind of diversion to break the boredom.  
  
I was drawn to Tom Riddle soon after his arrival. He was a strange, secretive boy. There was an aura of different glowing, pulsating around him as bright as the sun and as dark as a moonless night. As I observed him, I could sense an unshaped potential.  
  
He was used to being around muggles at the orphanage. Now he was in the midst of others in possession of magical skills far more advanced than his own. At first, he worked on learning better control of his skills. He was envious and intimidated by the skills of the others. However, he soon came to understand he had a skill exceeding that of those around him. His mind-controlling abilities surpassed that of the others, even those at the level of professor.  
  
My first observances of him using his powers were getting students to do things like picking their noses in front of people, trip someone else, or hit themselves. A few unfortunates got detention for making inappropriate comments in class. From there, he started into a darker, more sordid direction.  
  
Like most boys of his age, he seemed to have a fascination with girls. He started spending more and more time in the dining hall, library and common areas. His trick was to position himself across from a girl or girls. A moment later they would have their legs uncrossed and open so he could peer up their skirts. He would gaze with a youthful lust at their colorful panties, that is until the day he found his first girl who chose not to wear them.  
  
It was a week before the end of the school year. He was working his trick on a pretty girl named Shelly Hartwick. As her legs opened his heart and mind started racing so fast he almost broke concentration. I must admit to being amused. Shelly has a cream-colored pussy slit that was on open display for him to see. A fine layer of downy, light brown hair framed it in a most delectable manner. His young dick was surely throbbing as he rubbed it while enjoying the view. His expression said he wanted more.  
  
At the dawn of his second year, he decided to up his game. Within a few months, he had located several girls of all ages with a penchant for wearing nothing under their skirts. Hairy, hairless, blonde, black, red and brown, he was getting more than an eyeful from his unsuspecting victims. Still, he clearly yearned for more.  
  
By Christmas, he had mastered getting several of them to surreptitiously fondle themselves, or at least that is what they thought they were doing. Normally, they would slide a hand under a table and up their skirt. Often as not they would try to conceal their activities with a strategically-placed book. Most of the time, they subtly fondled their pussies until they opened up and were glistening in the candlelight with their virginal juices. A couple of the girls were bold enough to slide a finger or two, or even the handle of their wand inside their vaginas for some real action.  
  
He would stroke his cock through his pants as he carefully watched their expressions change from cautious to lust-filled as they fucked themselves, their wands working a different kind of magic than they learned in the classroom. On several occasions, these girls achieved a furtive orgasm before picking up their property and heading out to clean up in the lavatory. This spurred him on even further adventures.  
  
By his third year, he had identified four of his dozen or so viewing victims who seemed quite willing to totally bend to his will. One by one, he started coaxing them to a couple of remote locations in the castle where they eventually seemed to look forward to stripping naked and pleasuring themselves with reckless abandon.  
  
His first was Cassidy Fletcher from Newcastle, She was a 3rd year Gryffindor with a fetching smile, bright blue eyes, freckles head to toe and fiery red hair that would make a Weasley jealous. She would first strip off her blouse and bra so she could caress and squeeze her budding boobs, pinching her pinkish red nipples until they had hardened into fiery nuggets atop her young, blue-veined beauties. Then she would slide off her shoes and skirt so she could get down to the main event. It would start out slow, her fingers rubbing and stroking the lips of her red-haired slit. After a few moments, she would part her pussy lips to expose her eager, soaking wet cunt.  
  
Next, she would start rubbing a pair of fingers back and forth over her swollen clit, going faster and faster as her body began to heave and her breathing causing her to shake her breasts with great abandon. After a few moments of this, she would pull out her wand and plunge it into her beckoning hole. In and out it would go, faster and faster and faster as she moaned deliriously. Then, suddenly, she would arch her back and tense up. Gasping and babbling, she would start twitching as her juices flowed out, running down her wand onto her hands and the floor. Once finished, she would remove her wand from her steaming hole and lick and suck it clean before dressing and leaving.  
  
Zalika Kikuyu was born in London to parents who had immigrated from Nairobi, in Kenya. She was a 2nd year Hufflepuff whose family had migrated to London from Kenya. She had a slim body with pointy breasts. Her skin was the richest, darkest brown imaginable. She was much more straight forward in her personal play than Cassidy. She would quickly strip and lay down on the padded bench with her head on a cushion. One hand would pull open the hairless lips of her slit to show off a pussy that literally glowed bright pink against her skin which glistened like finely polished ebony the more her sweat added highlights to it in the torchlight.  
  
She would writhe in the throes of self- driven ecstasy while strumming back and forth across her clit, faster and faster until she began bucking and twitching like she was plugged into an electric outlet. As her tremors calmed she would reach up and grasp both of her small breasts and stroke and pinch her tiny, black nipples. This would set her off with another orgasm that frequently caused her to nearly pass out and fall off the bench. It would take a few moments for her to regain her composure, then she would redress and walk off with a very happy, satisfied expression on her face.  
  
Chandra Singh was a 3rd year Ravenclaw of Indian heritage from near Jaipur. She was blessed with light brown skin, black eyes and very thick, black hair on her head and between her legs. She was a slow starter, always spending a fair amount of time neatly placing her clothes in a stack before getting onto the bench. Once ready to get on with it, she would fondle her firm, growing tits for several moments, pinching and pulling on her coal-black nipples until they were firmly erect. It was only then that she laid back and moved things south. After some stroking and fingering of her slit, she would reach for her wand.  
  
Her wand had a large, carved nob on the end that seemed tailor-made for what she had planned. She would push it through her black bush and into her hidden hole with a mournful moan as she laid back and started stroking it in and out and an ever-increasing rhythm. It was impossible to see where her wand was disappearing as she frantically applied it. But her bouncing boobs were quite entertaining as she heaved and panted into two or three spastic, cramping orgasms. Like Cassidy, she seemed to enjoy the taste of her own juices. Her wand was always well cleaned by the time she had redressed and left.  
  
His last girl was another 2nd year Ravenclaw named Brynn Hughes from just outside of Cornwall in Wales. She was a chubby, short girl with a long braid of chestnut brown hair, brown eyes and full lips. She would strip down and plop back onto the cushioned bench ready for action. She would spread open her pussy with her left hand. In no time she would be stroking her right hand back and forth across her large, exposed clitoris so fast you could hardly see it before she erupted in erratic spasms accompanied by gasping groans. Often she moaned out the names of various boys at the school. Her relatively large tits, mostly due to her love of food, flopped around crazily during her exhibitions. She would occasionally suck and nibble on them before embarking on her customary second session of frantic masturbation.


	2. The Harem Master

Even with all of this to appease his voyeuristic lust, he continued to want even more. His mind manipulative skills continued to grow. It led him to plot even more depraved events. As the spring weather warmed, he started to take interest in occasionally moving things out of doors.  
  
By now he had eight girls under his control, having added a beautiful pair of 4th year Slytherin twins named Aurora and Willow Moore from County Cork in Ireland. They had long, straight, blonde hair, green eyes and lithe, flexible bodies. Unknown to Tom, they already enjoyed jointly pleasuring themselves before he discovered them. His first time bringing them to his secret third floor lair turned into quite a display. He had hoped to get a two for one show with them playing side by side. Instead, once stripped of their clothes, they began making out as they moved onto the soft cushiony bench.  
  
They knotted together, kissing and caressing each other until Aurora pulled up and slid downward so she could kiss and suckle on her sister’s firm breasts. Willow moaned and held Aurora’s head, tangling her hands in her luscious, blonde hair. After a few moments, Willow started moving south, kissing and licking her way across Aurora’s smooth belly. As she neared Aurora’s furry cunt, Aurora spread her legs to welcome her. Her back arched as the first licks pushed through her blonde patch and between her anxious pussy lips. Willow spread her pussy wide open and buried her face in the soggy, hot crevasse. With her knees raise and her hands frantically caressing Willow’s head, she heaved closer and closer to the orgasm she urgently needed. Then her green eyes rolled up inside her head as she started gasping out her sister’s name. “Willow. Willow, oh yes Willow. Yes. Yes. Oh-h-h-h yes-s-s-s-s.”  
  
The two of them rested for a few moments. Then they traded places to embark on a second session. As Aurora worked to turn Willow inside out, I noticed Tom in his customary hiding place. He usually watched quietly with a lustful expression. But something was different. I slid around behind him and got quite a surprise. He actually had his cock out and was excitedly pumping his hand up and down his shaft while watching his twins go to town. A moment later he was shooting his juices all over the floor and gasping while trying not to give away his presence. I had never seen him so animated.  
  
The girls finished a couple of minutes later in yet another gasping climax with Willow desperately urging her sister on. They hugged and kissed for a couple of minutes, sharing the tastes of each other that were spread across their faces. It was one of the wilder acts I had seen in my nearly 1,000 years as a ghost, but unbeknownst to me, I hadn’t seen anything, yet.  
  
His final disciple was a 5th year Hufflepuff girl from here is Scotland named Caitronia MacInnis. She had strawberry blonde hair surrounding a beautiful smile accented by sky blue eyes. She had the body of a Greek goddess. I don’t mean the classic beauties like Aphrodite or Eos, but the warrior athletes like Atalanta and Artemis. Stripped down, she was a shield, bow and arrows, and some blue woad paint away from being a warrior princess from the ancient tribes. It was easy to see how she could be the top-rated chaser in all of the school, and why she was also a professional prospect. Watching her massage her body while she strummed her slit with its blonde covering was almost magical. Her firm tits with their rock hard nipples hardly jiggled as she writhed in heated passion. Her abdominal muscles rippled and flexed as she strained to a vigorous completion. The cushion was always soaked with her pussy juices by the end.  
  
But Caitronia’s sexual desire went further than that, much further. Her top subject at Hogwart’s was Care of Magical Creatures. Her aptitude made it look like she had a future as a professor depending on how her quidditch aspirations worked out. Tom and I had a real surprise coming.  
  
It was a Saturday. Tom had been sitting near Caitronia at dinner, so I expected I would be seeing her in his lair before too long. This was his pattern. Sit near the girl he wanted to watch and work his mind tricks. Before long she excused herself from her friends and left the dining hall.  
  
Tom got up and left. I followed him up to the third floor where he got into his trusted hiding spot. A short while later I heard a shuffling of shoes and saw the silhouette of Caitronia coming our way, but what was it she had with her? As she neared, I recognized the shape of one of the school’s crups with its distinctive forked tail. What was she up to now?  
  
Caitronia sat down on the bench and started patting the crup, which she called Jack. As she continued petting him and telling him what a good boy he was she scooched forward onto the edge of the bench until Jack’s head was resting in her lap. Then she did something I had never seen in all of my years. She pulled up her skirt to expose her blonde pussy and started urging him to lick it as she pressed his head downward. Jack was more than happy to accommodate her. She spread her pussy lips to give him open access and leaned back moaning.  
Jack scrubbed her hot box with his large, flat tongue. Caitronia’s stomach began pumping in and out as her breathing got heavier and quicker. I thought she was about to explode, but she stopped him. She took him by his front legs and pulled him onto her. As she adjusted her position to match his height, I got a bit of a look at his doggy cock for the first time. It was long, thick, hard and quite red. It squirted several little bursts of juices as she aimed it into her hungry pussy.  
  
As soon as Jack gained initial entry he began humping until he had buried his doggy bone all the way inside her. The pace of his humping was quite frantic, his legs frequently leaving the ground as he pounded away. Caitriona was moaning incoherently, her legs high in the air and the muscle of her ass trying to hump back to meet him.  
  
They carried on for several moments before he stopped and they came apart. She immediately pulled him up on the bench and rolled him onto his back. This was the first time I could get a clear look at his red dog cock. It was, indeed, long and thick, but it also had a large ball at its base. Caitronia began licking it as it spurted more juices onto her face. Then she sucked it into her mouth and started fucking him with her face.  
  
This was the wildest thing I have ever witnessed in all of my years. I looked back at Tom and he was also overcome. I could tell he was pumping himself as hard as he could. His face showed the great strain and passion he was experiencing.  
  
After a couple of minutes, Caitronia released the suck hold she had on Jack’s cock. She got onto the floor on her hands and knees. Jack knew what to do. She fell forward onto her elbows, face on the floor as Jack drove his slippery rod deep into her anxious pussy. He pumped at an inhumanly fast pace as she squealed in unbridled ecstasy.  
  
They just stayed there, Caitronia moaning more about him being good and to keep pumping his doggy cum into her. It was confusing until I saw them come apart. It was then I realized that the big swelling I had seen at the base of his cock had been stuck inside her. A gusher of juices flowed out of her as Jack twisted around to lick himself clean. Her pussy farted several times, each fart accompanied by a burst of their combined juices.  
  
Caitronia eventually got up, straighten her clothes and started leading Jack back to from wherever they had come. Tom did the same, heading back to the Slytherin dormitories.  
  
Up until now, everything had occurred indoors. Tom’s first out of doors excursion brought all of the girls together on the shore of the Black Lake in the starry moonlight of a warm, late spring evening. They had never been together as a group. This was a first. But it did not seem to bother them. Tom’s control over them by now was so complete that they did as instructed without question. The biggest concern was the discipline they might get for being caught out of bed this late in the day.  
  
It started casually with small talk as Tom, always a master of hiding, watched them. Finally, Cassidy said they should go swimming. Aurora noted they did not have swimming suits. Caitriona said they did not need them. Besides, wet clothes could get them found out. Cassidy and Chandra started stripping down. The others quickly followed suit.  
  
The girls frolicked for several minutes before getting out. Willow cast a lumos spell that lit the area around them so they could get dressed, and so Tom could see the nude bodies of his collective. Brynn said they should do this again. They all agreed. It was hard to tell how much of this was Tom’s doing, and how much was their initiative.  
  
Two weeks later they found themselves together at the same spot on the shore. Before long they were all naked and wading into the water. As they enjoyed the water and the naughtiness of what they were doing Aurora and Willow started to make out. Slowly, the others paused to watch as they kissed and massaged each other’s breasts while their second hands were busy below the surface. They inched out of the water onto a grassy spot where they laid down and really started to get into their sensuous dance. The other girls gathered around to observe. Aurora and Willow reached up and pulled Chandra, then Cassidy into the action. Within moments all of the girls were wrestling in a carnal knot. One of them cast a nightlight spell so they could see better as they learned a whole new aspect of sexual behavior. Of course, Tom also benefited from the lighted situation.  
  
The scene went on for an hour as they all gave and received pleasure in ways they had never considered prior to then. Even the twins were over the top with joy since neither had ever been touched by anyone other than their sister. Tom was nearly overcome with the excitement of what he was viewing and the knowledge that he had orchestrated much of it.


	3. Dear Diary

Tom maintained his behavior in his 5th year. His thoughts of immortality and world domination that were so important to him in years past seemed sidetracked for the most part by his lustful voyeurism. He may well have never evolved into Lord Voldemort if it were not for the events following a chance meeting with a 3rd year Ravenclaw named Myrtle.  
  
In many ways, Myrtle was the female version of Tom. She was a friendless loner prone to melancholy. The two main differences were she did not relish this status. She wanted friends and popularity, but other students, especially one named Olive Hornby, made certain her life was miserable in ways only Severus Snape might be able to explain thanks to James Potter and friends several years later. The second difference was she lacked Tom’s potent mind-controlling powers.  
  
They both sat down at the same table to eat lunch at the same time without noticing the other. Startled, Myrtle immediately excused herself and started to get up. There was no way a handsome 5th year Slytherin was going to allow her to sit so near to him. Instead, Tom told her to stay. She sat back down, ecstatic, but at the same time scared to be actually asked to join someone, let alone someone like him.  
  
Tom seemed to have sensed her desperation and loneliness. He probably felt an opportunity to exploit it. They chatted a little during their meal, then they parted company.  
  
A couple of days later they passed in the hall. She smiled, hoping for acknowledgment. He returned the smile and said “Hello”. She had a happy expression following a big sigh. Someone actually seemed to like her, at least at a base level.  
  
They found themselves having lunch together again a few days later. Myrtle had seen Tom sitting alone and took a chance on joining him. He was quite willing. They struck up a conversation that turned to a discussion of their mutual status of being lonely and without friends. They seemed to be evolving into a strange pair bonded by an unfulfilled need of actual companionship.  
  
While Tom could certainly read much of Myrtle’s mind, she could not read what was in his head. The relationship took a turn a few days later when Myrtle asked Tom if he had ever had a girlfriend and whether or not he had ever kissed a girl. Tom said that he had done neither, and Myrtle admitted the same, although Tom surely knew as much. For reasons I cannot explain, Tom, who had never touched a girl despite all of the depravity he had caused and witnessed then leaned over and kissed her. She hesitated, then leaned in and they both shared their first romantic kiss.  
  
Their romance moved innocently along at an almost juvenile pace. While they kissed several times, they never made any move toward first or second base. They were too awkward, inexperienced and shy.  
  
That finally changed on the first day of spring when Myrtle asked Tom following a kiss if he wanted to do more, if he wanted to touch her as she loosened her tie and unbuttoned her top buttons. Tom hemmed a bit before saying that he would. Myrtle pulled off her tie and unbuttoned the rest of her blouse while pulling it out of her skirt. Tom cautiously put his right hand onto a bra-covered breast and started to squeeze it. Myrtle sighed and leaned in against his hand.  
  
They kissed as Tom fondled her breast. Myrtle reached around her back and unhooked her bra to give Tom access to her bare breasts. They were firm B cups with dark brown areola the size of a sovereign. Tom massaged them for some time before taking a chance and kissing and sucking on them. About that time they heard a noise. Fearing discovery, Myrtle quickly redressed and they head back to the castle.  
  
A couple of days later Tom took Myrtle to one of his favorite quiet spots in the castle which had been the scene of many a sordid display by members of his harem. In short order, she had removed her blouse and bra. Tom was enjoying them as she ran her hands inside his shirt and over his solid chest. A few minutes later he felt her hand pulling his hand down between her legs. There he found a moist, hairy twat aching for his touch.  
  
Tom explored her pussy with his fingers. Even though it was all new to him, he had a fair idea of what to do from watching his girls playing with theirs and their friends over the years. Myrtle was soon moaning with delirious pleasure from the first touches to her private region by anyone other than herself or her parents as a child. When Tom pushed his finger into her vagina she nearly swooned from the excitement.  
  
Myrtle moved a hand between Tom’s legs and was delighted to find a rigid shaft waiting for her. He started to hump as she stroked him through his pants. Wanting more, she worked to unfasten his belt and open his trousers. When her fingers finally touched his naked member it was like an electric shock passed through both of them.  
  
Tom kicked off his shoes and removed his trousers and underwear. Myrtle pulled off her skirt so she was completely naked. Tom removed his shirt and tie as Myrtle lay back on the floor, spreading her legs and beckoning him forward. He obliged, moving until his swollen rod was pushing through her wet hair, searching for the entrance to her forbidden treasure.  
  
Myrtle grasped his member and pulled him forward until he entered her. She had apparently lost her virginity sometime early in who knows what way. But she was apparently extremely tight and he was quite adequately endowed, so it was a bit of a struggle to get them firmly together.  
  
Tom began stroking in and out as she pushed back. They gave it their all as their breathing became more and more labored. The pace grew faster and faster, more and more forceful. I have witnessed many couples making love, but none with more urgent ardor. Suddenly they were both experiencing that moment of sweet, communal death they had often wondered possible for them. Tom collapsed, breathless, on top as Myrtle panted with great glowing satisfaction covering her face. All of the ugliness of life at Hogwarts seemed to have left her. I sensed Tom moving still further away from his plans for immortality and powers.  
  
Over the next couple of months, Tom spent less and less time with his harem and more and more time enjoying his carnal explorations with Myrtle. He also spent much less time studying texts and other things related to his interests in immortality and world domination.  
  
It was early June and the two of them had moved their affair to secluded spots out of doors. Today they were in a hidden alcove of rocks and trees on the shore of the Black Lake. Tom was on his back, rapt in lustful pleasure as Myrtle bounced up and down on his swollen member at a frantic pace. Her now ample breasts bounced wildly as Tom tried to capture and caress them. The look on her face was pure ecstasy.  
  
Tom’s back suddenly arched and his mouth gaped open as he strained to launch his essence into Myrtle’s fiery hole. Myrtle’s vaginal muscles gripped him like a powerful hand in a soft, velvety, wet glove. She squealed almost painfully as her orgasm electrified her body.  
  
She fell forward on to him. They lay there, still fastened together for several moments before Myrtle sat back up and looked at the still overcome with passion face below her.  
“I have something to tell you,” said Myrtle with a strange tone and pace to her voice.  
  
“What’s that?” replied Tom curiously.  
  
“I’m…uh…well…I’m pregnant”  
  
Tom tensed and moved to get up. “That’s…um…that’s like wow. How can we deal with it? We’ll get it trouble if anyone finds out.”  
  
“I don’t know. But we’ll figure it out. I love you and I am sure it will all be okay.”  
  
I could feel a great disturbance in Tom. This would exhilarate, even scare most anyone, but the feeling I was getting from Tom was bigger, more intense. It was more like desperation and panic than concern.  
  
Tom spent almost all of his free time over the next three days in the library and the chamber built by Salazar Slytherin that he had found under the school. He was very agitated and upset. Not being able to actually read his mind, I watched to see what he was up to.  
  
On the morning of June 13th, he saw Myrtle at breakfast. He asked her to meet him in the girl’s lavatory immediately after lunch. She agreed without question. At lunchtime, while it is true Olive Hornby was teasing her about her glasses, she did not run from the hall because of it. She used it as more of an excuse to escape to her meeting with Tom.  
  
I imagine she thought it a strange place for their meeting, but she took advantage of it by using a stall while waiting for Tom. She was humming in a cheerful manner when she heard the door open and someone begin using a strange language. She opened the stall door to see who it was. Maybe it was Tom playing a trick on her. All she saw was a big pair of glowing, yellow eyes as she died.  
  
She never knew of Tom’s betrayal of her. The story she tells about her death is a concoction made up to cover up her affair with Tom, the pain of losing him and her imagined future, and to avoid association with his future as Lord Voldemort. Tom used her death to create his first horcrux, his diary. I doubt that she knows these details, even to this day.


End file.
